Dichloromethane → HCID 12791050, compound

HRID 1155240Notes

Reaction equation

HRID 1155240 reaction equation
[CH3:1][CH2:2][O:3][CH2:4][CH2:5][O:6][C:7](=[O:21])[CH2:8][N:9]([C:15]([S:17][CH2:18][C:19]#[CH:20])=[O:16])[CH2:10][P:11](Cl)(Cl)=[O:12].C(Cl)Cl.[NH:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>C(OCC)C>[CH3:1][CH2:2][O:3][CH2:4][CH2:5][O:6][C:7](=[O:21])[CH2:8][N:9]([C:15]([S:17][CH2:18][C:19]#[CH:20])=[O:16])[CH2:10][P:11]([N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)([N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1)=[O:12]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 8083MorpholineHCID 20561467HCID 20561467, compound

Product 1

HCID 12791050HCID 12791050, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
25 °C

Procedure

(2-Ethoxy)ethyl-N-[(propargylthio)carbonyl]-N-[dichlorophosphinylmethyl]glycinate (10.5 g.; 0.028 mol.) was dissolved in 50 ml. of diethyl ether and 50 ml. of methylene chloride. To the solution was added a solution of morpholine (9.7 g.; 0.11 mol.) in 100 ml. of diethyl ether. The resulting mixture was stirred for 16 hours at 25° C., then filtered. The filtrate was washed with 3% ammonium hydroxide, brine, 5% hydrochloric acid and again with brine. The ether layer was separated, dried and concentrated in vacuo. The residue was purified using a silica gel column with acetonitrile as the eluent to yield (2-ethoxy)ethyl-N-[(propargylthio)carbonyl]-N-[bis(morpholino)phosphinylmethyl]glycinate, dihydrate as an oil (nD25 =1.5200) having the following analysis:

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with 3% ammonium hydroxide, brine, 5% hydrochloric acid and again with brine
  3. customThe ether layer was separated
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified

Sources & evidence

ORD record
ord-a27df74707bf4f799639eedce6e9957f
Source dataset
uspto-grants-1981_11
Patent number
US04300942

Reaction notes

Loading…